Did Timberman this year, looking for a comparison on the bike between Timberman and Quassy in terms of difficulty and climbing. Im a BOPer looking for a challenge to train towards. Thx.
Have not done the actual Quassy race, but planning on it for 2011 as a tune up for LP. I do train on those roads a lot since the start is less than an hour from my house…all you have heard about it being tough is true. Very little flat land around there. I do not know about Timberman. Do both…plenty of time between them. 
Sinkin - We’re doing Cedar Point full Rev (140.6) in September in lieu of Timberman. I’ll be back to Timberman but I want my 140.6.
I have done Timberman and did the Quassy Oly, but did motorcycle duty on the half. Quassy is 1000+ more feet total climbing on the bike.
And forget about the bike… Fear the run! The Quassy Oly had 1400 ft of climbing on the run, and I think the half is around 2400. Quassy is one of the toughest in the US. Savageman is Tougher, and there may be a few others
I did both this year. Quassy is much more difficult for both the bike and the run. I did a 4:57 at Rev3 and a 4:39 at Timberman.
So far, Rev3 is the hardest 70.3 race I have done. Hell, even Lake Placid seemed easier.
I did Nutmegman the past 2 years and it shares the same terrain as Quassy. Probably a race you might want to consider a road bike on. I was climbing and descending all the time. Not alot of terrain for aero IMHO. But Timberman, while its bookended with hills that middle section is flat out fun. I wouldnt compare the 2 bike courses. But Id say the terrain around Quassy is going to be MUCH more difficult than the terrain at Timberman.
cheers
S.